Acadesine (CHEM018695)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:27:42 UTC
Update Date2016-11-09 01:15:51 UTC
Accession NumberCHEM018695
Identification
Common NameAcadesine
ClassSmall Molecule
DescriptionAICA-riboside is a purine nucleoside analog with anti-ischemic properties that is currently being studied (Phase 3) for the prevention of adverse cardiovascular outcomes in patients undergoing coronary artery bypass graft (CABG) surgery. It is being developed jointly by PeriCor and Schering-Plough. AICA-riboside has been granted Orphan Drug Designation for B-CLL in the EU.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamideChEBI
5-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamideChEBI
5-Amino-1-beta-ribofuranosyl-imidazole-4-carboxamideChEBI
5-Amino-1-ribofuranosylimidazole-4-carboxamideChEBI
5-Amino-1beta-D-ribofuranosylimidazole-4-carboxyamideChEBI
5-Amino-4-imidazolecarboxamide ribofuranosideChEBI
5-Aminoimidazole-4-carboxamide ribonucleosideChEBI
AcadesinaChEBI
AcadesinumChEBI
AIC-ribosideChEBI
AICArChEBI
EC number 220-097-5ChEBI
GP 1-110ChEBI
GP-1-110ChEBI
N(1)-(beta-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamideChEBI
5-Amino-1-b-D-ribofuranosyl-4-imidazolecarboxamideGenerator
5-Amino-1-β-D-ribofuranosyl-4-imidazolecarboxamideGenerator
5-Amino-1-b-D-ribofuranosylimidazole-4-carboxamideGenerator
5-Amino-1-β-D-ribofuranosylimidazole-4-carboxamideGenerator
5-Amino-1-b-ribofuranosyl-imidazole-4-carboxamideGenerator
5-Amino-1-β-ribofuranosyl-imidazole-4-carboxamideGenerator
5-Amino-1b-D-ribofuranosylimidazole-4-carboxyamideGenerator
5-Amino-1β-D-ribofuranosylimidazole-4-carboxyamideGenerator
N(1)-(b-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamideGenerator
N(1)-(Β-D-ribofuranosyl)-5-aminoimidazole-4-carboxamideGenerator
AICA RibonucleosideHMDB
Z-RibosideHMDB
ArasineHMDB
AICA RibosideHMDB
ARA-100HMDB
Aminoimidazole carboxamide ribonucleosideHMDB
5-Aminoimidazole-4-carboxamide ribosideHMDB
AICA RibofuranosideHMDB
1-Ribosyl-4-carboxamido-5-aminoimidazoleHMDB
5-Aminoimidazole-4-carboxamide 1-ribofuranosideHMDB
ARA 100HMDB
5-Amino-1-β-D-ribofuranosyl-imidazole-4-carboxamideHMDB
5-Amino-1-beta-D-ribofuranosyl-imidazole-4-carboxamideHMDB
5-Amino-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamideHMDB
5-Amino-1-beta-D-ribofuranosyl-1H-imidazole-4-carboxamideHMDB
1-Β-D-ribofuranosyl-5-amino-4-imidazolecarboxamideHMDB
1-beta-D-Ribofuranosyl-5-amino-4-imidazolecarboxamideHMDB
5-Amino-1-ribosyl-4-imidazolecarboxamideHMDB
5-Amino-4-imidazolecarboxamide ribosideHMDB
5-Aminoimidazole-4-carboxamide 1-(β-D-ribofuranoside)HMDB
5-Aminoimidazole-4-carboxamide 1-(beta-D-ribofuranoside)HMDB
AcadesineHMDB
AcadraHMDB
NSC 105823HMDB
5-Aminoimidazole-4-carboxamide-N-ribofuranosideHMDB
AICA-ribosideHMDB, ChEBI
Chemical FormulaC9H14N4O5
Average Molecular Mass258.231 g/mol
Monoisotopic Mass258.096 g/mol
CAS Registry Number2627-69-2
IUPAC Name5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazole-4-carboxamide
Traditional Nameacadesine
SMILESNC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChI IdentifierInChI=1S/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m1/s1
InChI KeyRTRQQBHATOEIAF-UUOKFMHZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as imidazole ribonucleosides and ribonucleotides. These are organic compounds in which the C-1 of a ribosyl moiety is N-linked to an imidazole ring. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety. This class does not contain benzimidazole nucleosides and nucleotides.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassImidazole ribonucleosides and ribonucleotides
Sub ClassNot Available
Direct ParentImidazole ribonucleosides and ribonucleotides
Alternative Parents
Substituents
  • Imidazole ribonucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Aminoimidazole
  • Monosaccharide
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Organic oxygen compound
  • Primary amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility25 g/LALOGPS
logP-1.8ALOGPS
logP-2.6ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)12.45ChemAxon
pKa (Strongest Basic)4.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area156.85 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity58.27 m³·mol⁻¹ChemAxon
Polarizability24.01 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-9430000000-675bbf40b4a04dfec20fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0kg9-8779500000-a9c8984b44d96de53e39Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-3900000000-4c2f4a4576966bfbb5adSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-4900000000-097651e11df9c45f361aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-1900000000-da8f0cdc0fe28d0b25f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0920000000-e19e90d3ffc85e386592Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0a4i-0390000000-1e03403462be9141bb3cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004l-7900000000-336109197f247d6945e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-c060e9f97f31c1927d3cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-01ow-9300000000-6152aeb5ea4b0b762a76Spectrum
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-0a4i-0390000000-32f75647d0ba48153b0fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-77c5ec151cbf46016e64Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-cf8f7c2e1ad089e87127Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0910000000-a101f45b587a72aeaa23Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0920000000-72894dd16bb8e0005828Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-3900000000-9434ee6ac3a8a4661a5bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0940000000-ea93dd3a2de5f795b019Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1900000000-7fe87a0ee05719a96e28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9800000000-1e5c3421d6db24a495feSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-3790000000-19ce0e4eb5316822db20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-4910000000-be0aa62606b149cdb5deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9100000000-d85d74dc8734fb950d49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900000000-834f36e8dacd15862554Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-4900000000-51b6a467a9f7d0152dceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-8900000000-5457862ae822930e3810Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-4920000000-d03806b1503a73d09df4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9200000000-e42429a50879bca0a959Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04944
HMDB IDHMDB0062179
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAcadesine
Chemspider IDNot Available
ChEBI ID28498
PubChem Compound ID17513
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Marie S, Heron B, Bitoun P, Timmerman T, Van Den Berghe G, Vincent MF: AICA-ribosiduria: a novel, neurologically devastating inborn error of purine biosynthesis caused by mutation of ATIC. Am J Hum Genet. 2004 Jun;74(6):1276-81. Epub 2004 Apr 26.
2. Mullane K: Acadesine: the prototype adenosine regulating agent for reducing myocardial ischaemic injury. Cardiovasc Res. 1993 Jan;27(1):43-7.
3. Gruber HE: Acadesine: preclinical overview. Adv Exp Med Biol. 1994;370:423-6.
4. Engler RL: Harnessing nature's own cardiac defense mechanism with acadesine, an adenosine regulating agent: importance of the endothelium. J Card Surg. 1994 May;9(3 Suppl):482-92.
5. Melton SM, Moomey CB Jr, Ragsdale DN, Trenthem LL, Croce MA, Fabian TC, Proctor KG: Acadesine during fluid resuscitation from shock and abdominal sepsis. Crit Care Med. 1999 Mar;27(3):565-75.
6. Guigas B, Sakamoto K, Taleux N, Reyna SM, Musi N, Viollet B, Hue L: Beyond AICA riboside: in search of new specific AMP-activated protein kinase activators. IUBMB Life. 2009 Jan;61(1):18-26. doi: 10.1002/iub.135.
7. Drew BG, Kingwell BA: Acadesine, an adenosine-regulating agent with the potential for widespread indications. Expert Opin Pharmacother. 2008 Aug;9(12):2137-44. doi: 10.1517/14656566.9.12.2137 .
8. Van Den Neste E, Van den Berghe G, Bontemps F: AICA-riboside (acadesine), an activator of AMP-activated protein kinase with potential for application in hematologic malignancies. Expert Opin Investig Drugs. 2010 Apr;19(4):571-8. doi: 10.1517/13543781003703694.
9. Schlimme E, Schneehagen K: Ribonucleosides in human milk. Concentration profiles of these minor constituents as a function of the nursing time. Z Naturforsch C. 1995 Jan-Feb;50(1-2):105-13.
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=17513706
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=17706943
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=18090925
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=18457469
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=18671468
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=20185792
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=20367195
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=21244913
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=23228986
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24303202
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=24519895
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=24778186
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=8227467
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=8458030